N-[(2R,3R,4R,5R,6S)-2-Benzyloxy-4-hydroxy-6-methyl-5-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-acetamide

Base Information

Chemical Name:N-[(2R,3R,4R,5R,6S)-2-Benzyloxy-4-hydroxy-6-methyl-5-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-acetamide
CAS No.:174151-47-4
Molecular Formula:C₂₂H₂₈N₂O₆S
Molecular Weight:448.54
Hs Code.:

Synonyms:N-[(2R,3R,4R,5R,6S)-2-Benzyloxy-4-hydroxy-6-methyl-5-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-acetamide

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Chemical Property of N-[(2R,3R,4R,5R,6S)-2-Benzyloxy-4-hydroxy-6-methyl-5-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-acetamide

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Technology Process of N-[(2R,3R,4R,5R,6S)-2-Benzyloxy-4-hydroxy-6-methyl-5-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-acetamide

There total 5 articles about N-[(2R,3R,4R,5R,6S)-2-Benzyloxy-4-hydroxy-6-methyl-5-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 39.0%

: 127-65-1
chloroamine-T

: 174151-46-3
benzyl 2-acetamido-2,3,4,6-tetradeoxy-α-L-threo-hex-3-enopyranoside

: 174151-48-5
N-[(2R,3R,4R,5R,6S)-2-Benzyloxy-5-hydroxy-6-methyl-4-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-acetamide

: 174151-47-4
N-[(2R,3R,4R,5R,6S)-2-Benzyloxy-4-hydroxy-6-methyl-5-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: With osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride; In chloroform; water; tert-butyl alcohol; at 60 - 70 ℃; for 72h;
DOI:10.1016/0008-6215(95)00291-X

Reference yield:

: 76404-33-6
Benzyl-2,3,6-tridesoxy-α-L-threo-hex-2-enopyranosid

: 174151-47-4
N-[(2R,3R,4R,5R,6S)-2-Benzyloxy-4-hydroxy-6-methyl-5-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 1.) CH₂Cl₂, RT, 5 min, 2.) CH₂Cl₂, 0 deg C

2: 68 percent / various solvent(s) / 5 h / 160 °C

3: 83 percent / NaOH / ethanol / 2 h / 80 °C

4: 100 percent / pyridine

5: 39 percent / OsO₄ / TEBA / H₂O; 2-methyl-propan-2-ol; CHCl₃ / 72 h / 60 - 70 °C

With pyridine; sodium hydroxide; osmium(VIII) oxide; sodium hydride; N-benzyl-N,N,N-triethylammonium chloride; In ethanol; chloroform; water; tert-butyl alcohol;
DOI:10.1016/0008-6215(95)00291-X

Reference yield:

: 174151-45-2
benzyl 2-amino-2,3,4,6-tetradeoxy-α-L-threo-hex-3-enopyranoside

: 174151-47-4
N-[(2R,3R,4R,5R,6S)-2-Benzyloxy-4-hydroxy-6-methyl-5-(toluene-4-sulfonylamino)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / pyridine

2: 39 percent / OsO₄ / TEBA / H₂O; 2-methyl-propan-2-ol; CHCl₃ / 72 h / 60 - 70 °C

With pyridine; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride; In chloroform; water; tert-butyl alcohol;
DOI:10.1016/0008-6215(95)00291-X